Daniel Caesar had a phenomenal 2017. The Oshawa-bred R&B singer-songwriter’s debut studio album, Freudian, earned two Grammy nominations; he played the late-night TV circuit; he sold out five straight shows at the Danforth Music Hall; and his face was suddenly plastered on billboards, bus shelters and video screens above Yonge-Dundas Square. This past weekend, Caesar (born Ashton Simmonds) capped off a killer year with one of the most sparkling endorsements imaginable: not one but two spots on Barack Obama’s list of favourite songs of 2017. Here, eight things you should know about Toronto’s next biggest musical export.

Music runs in the family

1Caesar’s father, the gospel singer Norwill Simmonds, released his first album as a high schooler in Jamaica. According to Caesar, his dad got ripped off by his reps. “He made, like, $17 off the recording,” Caesar told Nardwuar, which caused Simmonds to be cynical when his son’s career began to blossom. “He doesn’t mess with the music industry.”

He got kicked out of high school

3Caesar attended a private Christian high school in Oshawa and, funny enough, failed choir class in grade 10, the year he discovered pot and Pink Floyd. He was expelled a year later for selling “like two grams” of weed to a classmate.

He was homeless for a while

4Caesar moved to Toronto to pursue music after he finished high school (he was home schooled after being expelled). Trouble was, he had no place to stay. He crashed on friends’ couches after late-night dishwashing shifts most nights, but at least once spent the night sleeping in Trinity Bellwoods Park when he had nowhere else to go.

He’s a cinephile

5Caesar talks about his love of film in an amusingly creepy interview with Nardwuar. Casablanca was a memorable watch. “I was very intrigued by it,” he said. “I wrote a song about it the same day [I watched it].” But Pulp Fiction is his favourite, even if he ruined it for himself with repeated viewing. “There was a time where I would watch it like 30 times in a row,” he told Noisey.

His career is decidedly DIY

6Caesar released Freudian on Golden Child Recordings, a record label he founded with the help of producers Matthew Burnett and Jordan Evans, frequent Drake collaborators. That’s not because other labels weren’t interested. “Why would I want to give my baby, my creation, this thing I made over to [a label] when we don’t have the same values?” he told Now Magazine. “As soon as you sign, you give over your ideas, your potential, to somebody else to do how they see fit. You’re no longer the big boss.”

Feeling @DanielCaesar music on a legit physical level.. if you haven’t you must get involved right now.

He got vocal tips from Mary J. Blige

8Mary J. Blige is also a fan. Caesar co-wrote her song “Telling The Truth.” During the session, “Mary told me the weirdest shit I ever heard,” he told Now. “She said to get a pot of hot water and put gummy bears in it and melt it down and drink it. Apparently that’s good for your throat.”

He’s responsible for a new marriage proposal trend

9This was not the first (or last) time someone proposed at one of Caesar’s shows.

Photo courtesy of the Drake Hotel

He still hasn’t lived his dream

10Caesar used to live down the street from the Danforth Music Hall, where he capped his 2017 tour in December. His original goals were more modest. He told Nardwuar that early in his career he said to his friends, “Yo, one day I’m gonna play the Drake hotel, and it’s gonna be crazy.” He still hasn’t performed there.